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An Insider’s Guide to September Events in the Hudson Valley

Boscobel View | Photo by Jamie Martorano

Hudson River tourism directors share their top picks for places to go, sights to see, and things to do throughout September.

We’ve said it before and we’ll say it again. There are a ton of things to do in the Hudson Valley each month. Even in the face of the coronavirus, there exist dozens upon dozens of ways to experience the best of what the region has to offer. While they might not be traditional per se (haunted walking trails, anyone?), they are engaging, entertaining, and 100-percent #flattenthecurve-approved.

To help scout out the best events in the Valley, we reached out to local tourism directors from Albany to Westchester for their top picks for things to do. Check out their selections, then get planning!

Albany County

Discover Albany President and CEO Jill Delaney shares her top recommendations for the month.

Capital District Scottish Games

Altamont Fairgrounds, Altamont
September 4, 8 a.m. – 10 p.m.

Albany County hosts one of the longest-standing cultural traditions across the state. The Capital District Scottish Games are an honest-to-goodness hop across the pond. Experience Highland dancing, a Scottish breed dog show, pipe bands, athletic competitions, and tons of traditional folk artists.


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Albany Riverfront Jazz Festival

Jennings Landing, Albany
September 10, 12-8 p.m.

Late-summer days along the Hudson River are unparalleled. The Albany Riverfront Jazz Festival showcases local musicians at scenic Jennings Landing. It’s a great event to catch some critically acclaimed up-and-coming artists. Festivities culminate in a dazzling fireworks spectacle above the water.


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Pearl St, Albany
September 18, 1 p.m.

Ready to jam out to more outdoor music? Downtown Troy BID hosts this free festival every year along Pearl St. Bounce between two main stages and catch a slew of modern acts. All the yogis out there can join Yogapalooza, a mass session. Of course, there are also plenty opportunities to sample some of the Capital Region’s finest cuisine from dozens of street vendors.

Albany Book Festival

University of Albany, Albany
September 25

Calling all readers! This yearly literary celebration returns in person to the University of Albany. Interact with a lineup of diverse voices who write in nearly every genre. From nationally acclaimed authors to up-and-coming Hudson Valley writers, everyone in attendance is passionate about the medium.

Columbia County

Read up on Columbia County Tourism’s highlights for things to do in the Hudson Valley this month.

Columbia County Fair

Photo courtesy of Columbia County Tourism

Columbia County Fair

32 Church Street/State Route 203, Chatham
September 1-6

County fairs returned to the Hudson Valley this year, and it has been glorious. Keep the party going in Chatham the first week of September. Demolition derbies, monster truck shows, magic shows, rodeos, and a massive lineup of bands provide thrilling entertainment. Don’t miss fair classics like the “Hot Dog” pig races or the “Painted Pony” rodeo. Come hungry and dig into all things deep-fried and on a stick.


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Good People by David Lindsay-Abaire

The Theater Barn, New Lebanon
September 9-19

New Lebanon’s The Theater Barn stages Good People in a scenic destination. This show won a Tony Award for Best Play in 2016, and tackles issues of class in Boston’s south end. For every tough and tender moment, there are also a ton of laughs as the protagonist Margie navigates her hopes and fears.

Dutchess County

Dutchess Tourism President and CEO Melaine Rottkamp shares her top recommendations for the month.


Hudson Valley Hot Air Balloon Festival | Photo by Alicia Oltz

Hudson Valley Hot Air Balloon Festival

Tymor Park, Union Vale
September 3-5

Explore one of the Hudson Valley’s many time-honored traditions to celebrate the arrival of fall. Witness the magic of over 75 hot air balloons launching into the sky at the festival’s 30th anniversary. Thousands of visitors gather for the spectacle. A few highlights include fireworks every night, tethered hot-air balloon rides, helicopter tours, live music, and the majestic hot-air balloon illumination moon glow.


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Oktoberfest! at Germania

Germania, Poughkeepsie
September 10-12

Prost! Oktoberfest season is upon the Hudson Valley. Poughkeepsie’s Germania is a 170-year old German-American preservation society that hosts an authentic Oktoberfest every year. While you’re sipping pilsners and lagers, dance to music from bands like the Bratwurst Boys, the Adlers Band, and the Germania singers. Be sure to catch a performance of traditional German dance, and don your best dirndl or lederhosen. 

Chef Diana

Photo courtesy of Dutchess Tourism, Inc.

Hudson Valley Wine & Food Fest

Dutchess County Fairgrounds, Rhinebeck
September 11-12

Taste your way through the region’s finest wineries, distilleries, and cideries. More than 60 producers showcase their very best at this Rhinebeck to-do. Pair beverages with lunch from one of the many local food trucks and vendors set up at the Dutchess County Fairgrounds. Nearly a hundred purveyors in total will be in attendance. Plus, shop crafts and wares to deck out your home kitchen. Visitors can learn about wine from Hudson Valley vintners and food from many cooking demonstrations and seminars throughout the weekend.

Greene County

Look no further for the coolest attractions and activities in Greene County during the month.

Riedlbauer’s Resort Presents Nussy’s Oktoberfest

Riedlbauer’s Resort, Round Top
September 11

Enjoy authentic Germain cuisine at Riedlbauer’s Resort in Round Top. Its take on Oktoberfest at Nussy’s Bier Garten features live music, dancing, and a bit of Hudson Valley history. The mountaintop resort offers breathtaking views and a stunning biergarten.

Catskill Mountain Thunder Motorcycle Festival

Blackthorne Resort, East Durham
September 15-19

Calling all adrenaline junkies! One of the largest motorcycle festivals in New York State arrives at East Durham’s Blackthorne Resort. Kick things off on Wednesday night with a pub crawl and return Thursday for a pre-show auction. Visitors will watch stunt shows, rodeo games, and a bike show with cash prizes.

Hudson River Skywalk Arts Festival

Rip Van Winkle Bridge, Catskill
September 19

One of fall’s biggest art festivals hosts vendors above the Hudson River. Take a stroll on the historic pedestrian bridge connecting the homes of legendary Hudson River School artists Thomas Cole and Frederic Church, then stop by the park at the bridge entrance for shopping, art lessons, and music. It’s all surrounded by the scenic backdrop of the Great Northern Catskills.

Orange County

Check out Orange County Tourism Director Amanda Dana’s selections for the best things to do this month.

Ranger Adventures Night Hike

Sterling Forest State Park, Tuxedo
September 18, 5:30 p.m.

What’s more magical than a night under the stars in the Hudson Valley? Embark on a nighttime hike through Sterling Forest State Park, with the Manhattan skyline in the distance. Bring flashlights and headlamps, and prepare for a one-of-a-kind evening.


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’80s New Wave Dance Party With the Georgia 5

Tin Barn Brewing, Chester
September 12, 2 p.m.

The ’80s are back. Leg warmers, “Members Only” jackets, and brightly colored attire mark the expected getup at Tin Barn Brewing’s New Wave Dance Party. Georgia 5, the Hudson Valley’s signature ’80s band, fuels the party with throwback jams. Tin Barn’s newly opened deck is the perfect spot to cut a rug.

4th Annual Oktoberfest

Sugar Loaf Engine Company, Chester
September 19, 3-8 p.m.

Mark your calendars, Hudson Valley! Oktoberfest is happening in Chester. Throughout the day, attendees can dig into hot dogs, bratwurst, soft pretzels, and more while sipping on German brews. (Hint: try the Spaten Oktoberfest on tap.) Cornhole, giant Jenga, and other games are available for playing.

Renaissance Fair Duel

Photo courtesy of New York Renaissance Faire and Deborah Grosmark

New York Renaissance Faire

600 Route 17A, Tuxedo
All month long

Step into a world of chivalry, jousting, royal feasts, and other festivities. The New York Renaissance Faire transports guests to Elizabethan England every Saturday and Sunday. Devour savory treats, witness breathtaking performances, and shop at an authentic artisan marketplace. Any trip to the Renaissance Faire wouldn’t be complete without a seat at the jousting tournament. Cheer on a knight and observe displays of bravery and strength. Season passes are only $175, if the 16th century lifestyle suits you. During the weekend of September 11 and 12, come dressed as any era for Time Travelers’ weekend. Scallywags and nautical outlaws alike gather the following weekend for Pirate Weekend.

Putnam County

Read up on Putnam County Tourism Director Tracey L. Walsh’s picks for things to do this month.


Boscobel View | Photo by Jamie Martorano

Brews With Views

Boscobel House and Gardens, Garrison
September 11, 2-6 p.m.

Nothing pairs better with a craft beer than gorgeous Hudson Valley views. Hops on the Hudson moves its annual party to Boscobel House and Gardens for an unbelievably scenic setting. Over 30 brewers and cider-makers supply more than 100 tap pours. Get tickets online and in advance for a 20-percent discount.

Putnam History Museum’s Annual Lawn Party

William Kemble Home, Cold Spring
September 18, 4 p.m.

Curious about how the other half lived in the 1800s? Head to the gracefully restored William Kemble Home for Putnam History Museum’s annual lawn party. Step into a bygone era, and don period-accurate clothing if you’re able. Take a tour of the house, meet President Abraham Lincoln, and explore the life of Kemble, one of the founders of the West Point Foundry. Enjoy refreshing drinks and canapes until the sun goes down.

Blues & BBQ Festival

Patterson Fire Dept, Patterson
September 18 & 19 

Looking for things to do in the Hudson Valley this weekend? One of the few summery events remaining before autumn takes over, the Patterson Blues and BBQ Festival is a great way to spend the weekend. Finger-lickin’ barbecue fuels two full days of live music. Sample fall-off-the-bone smoked ribs, Oktoberfest-themed bratwurst, and so much more. Each day features five separate acts to take the stage.


Photo courtesy of Putnam County Tourism

Open House on the Farm

Tilly Foster Farm, Brewster
September 25, 11 a.m. – 3 p.m.

Tilly Foster Farm welcomes fall in a grand manner with a fun-filled “open house.” With fresh hot apple cider in hand, explore the 199-acre Brewster property or the connecting nature trails. Grilled corn and cider donuts are the delicacies of choice. Plus, cute animals, antique tractors, and a nature-themed scavenger hunt keep the kids entertained. Entry is completely free, but requires an online pre-registration. Visit the farm starting September 4 to experience the Collaborative Concepts outdoor art exhibit. Large-scale sculpture art will line the site until the beginning of October.

Rockland County

Take a browse through the top picks of things to do in Rockland County this month.


Photo courtesy of Rockland County Tourism

11th Annual Highlands Bluegrass Festival

Harmony Hall-Jacob Sloat House, Sloatsburg 
September 12, 1-5 p.m.

Feeling the spirit of the season? Autumn’s soundtrack is folk music and bluegrass, without a doubt. Grab a spot on the great lawn at Harmony Hall-Jacob Sloat House in Sloatsburg for the Highlands Bluegrass Festival. Cole Quest & The City Pickers, led by the grandson of folk legend Woody Guthrie, The Eugene Tyler Band, and Blue Plate Special perform music that will make the crowd move. Sip craft pours in the beer garden, and snack on local specialties between sets. Tickets cost $10 per person.

Nyack’s Septemberfest Street Fair

Main St & Broadway, Nyack
September 12, 10 a.m. – 5 p.m.

Nyack’s Main St and Broadway shut down for this massive street fair. Peruse more than 200 vendors, including food trucks, handmade jewelry tents, arts and crafts stations, and tons of family fun.

Food Crawl

Photo courtesy of Rockland County Tourism

Flavors of Haverstraw Food Crawl & Beer Garden

Main St & Broadway, Haverstraw
September 19, 1-5 p.m.

Experience the diverse cuisine of downtown Haverstraw with this classic late-summer food crawl. More than a dozen local restaurants supply fan-favorites and exotic specials. Plus, plenty of Hudson Valley brews are available at the NY Craft Beverage Garden. Dine your way down Main St for $3-$6 plates.

Suffern Street Fair

Lafayette Ave, Suffern
September 19, 10 a.m. – 5 p.m.

Suffern’s street fair features a massive amount of family-friendly activities. Compete in mini-golf, brave the bumper car gauntlet, and sign up for free fitness classes. From bounce houses to face painting and more, there’s plenty to do on Lafayette Ave.

Ulster County

Read up on Ulster County Tourism’s event highlights for the month.

Woodstock-New Paltz Arts & Craft Fair

Ulster County Fairgrounds, New Paltz
September 4, 5, & 6

Take part in this absolutely iconic Ulster County event. The Woodstock-New Paltz Arts & Craft Fair started as a family business in the 1980s and remains family-run to this day. Connect with artisans and craftspeople from across the United States. Peruse ceramics, jewelry, glass, metal, leathers, and more. In the specialty foods category, visitors to New Paltz can sample gourmet pickles, raw honey, handmade strudel, and flavored nuts, to name a few. More than 200 juried artists display their work at the fairgrounds as well.

Apple Festival

Town of Esopus United Methodist Church, Port Ewen
September 25, 8 a.m. – 3 p.m.

Who’s hungry for Hudson Valley apples? Fall is all about treats featuring the native fruit, and the Town of Esopus gathers a vast collection of the good stuff. Nab fresh-baked pies, apple pancakes, and lots of apple desserts ala mode. Whole bags of apples are also available for purchase for any home bakers in attendance.

Woodstock Film Festival | Photo courtesy of Ulster County Tourism

Woodstock Film Festival

Multiple locations
September 29 – October 3

A favorite fall happening in the Hudson Valley, the Woodstock Film Festival keeps local film aficionados happy with its programming. More than 150 films screen throughout the Hudson Valley. Special programming includes drive-in showings, Q&As with filmmakers, and panels with industry leaders. Head to the website to scout out the full lineup.

Courtesy of Headless Horseman Haunted Attractions and Ulser County Tourism

Photo courtesy of Headless Horseman Haunted Attractions and Ultser County Tourism

Headless Horseman Haunted Attractions

Headless Horseman Haunted Attractions, Ulster Park
September 25 – October 31

The “#1 Haunted Attraction in America” returns in a big way. This year, spectators will get closer to the horror than ever before. Visitors will walk the haunted woods where the Horseman lurks, without the safety of the typical hayride. Eight other attractions including spooky motels, monster-filled greenhouses, haunted corn mazes, and more bring the scares. Opening night features discounted tickets, and reservations are strongly encouraged.

Westchester County

Discover the hottest happenings according to Westchester County Tourism this month.

Big Performances at The Capitol Theatre

The Capitol Theatre, Port Chester
September 14-15, & 22

Throwback jams are coming to Westchester. First up is ’90s superstar Sheryl Crow, who performs a two-night run on September 14 and 15. Later in the month, on September 22, punk rocker Billy Idol takes the stage for an unforgettable performance. Reserve your tickets online.

This is a view of the Great Jack O’Lantern Blaze at Van Cortlandt Manor in Croton-on-Hudson on October 12, 2015. (Photo by Tom Nycz) / Courtesy of Historic Hudson Valley

The Great Jack O’ Lantern Blaze

Van Cortlandt Manor, Croton-on-Hudson
Beginning September 17

The Blaze is back! The Hudson Valley’s electrifying Halloween event fills the grounds at Van Cortlandt Manor with more than 7,000 illuminated jack o’ lanterns in a variety of haunting shapes and sculptures. To ensure social distancing, advance reservations are required. The show burns through the fall season, kicking off Friday, September 17 and wrapping November 21.

Westchester Wine and Food Festival

Locations throughout Westchester County
September 21-26

Take a tour of Westchester’s finest eats in September. This week-long event from our sister publication Westchester Magazine highlights the very best of craft beverage and delicious dining with a full lineup. Firstly, explore Italian wines at Kanopi Restaurant and Event Space on the 42nd floor of the magnificent Opus Hotel in White Plains. Party on Playland Park’s pier in Rye, and sample a variety of goods from local restaurants and food trucks. Westchester County’s top bartenders go head-to-head in the Bartender Shake-Off. Later in the week, the Burger and Beer Bash does comfort food the best at Kensico Dam Plaza, and the Wine Collector’s Dinner at X20 Xavier’s on the Hudson delights with fine dining. Finally, the entire week climaxes with the Grand Tasting Village. Endure the gastronomic gauntlet of Valhalla with over 40+ local restaurants and more than 200 wines and spirits represented. Buy tickets online today to individual events.

If you’re hungry for more, the beerier-than-ever Hopfest returns September 25. This celebration of Oktoberfest also features wine, local food trucks, and a bit of Hudson Valley history.

Related: The Best Events & Fests to Hit in the Hudson Valley This Fall

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